Gretchen Whitmer, the dynamic governor of Michigan and author of the bestselling 'True Gretch,' shares her insights on leadership and resilience while reflecting on the political landscape as co-chair of the Harris-Walz campaign. She discusses her journey of taking on Trump and the significance of grassroots engagement in swing states. Meanwhile, Illinois Governor JB Pritzker takes Jordan Klepper on a humorous tour of Chicago, highlighting its cultural richness and political importance ahead of the Democratic National Convention.

Former President Barack Obama and former First Lady Michelle Obama offer compelling insights at the DNC. Michelle passionately supports Kamala Harris, emphasizing perseverance in politics. Barack calls for unity and action, reflecting on privilege in the political landscape. Illinois Governor JB Pritzker shares personal experiences from his vice presidential vetting, highlighting pride in his immigrant roots. The contrasting tones of the Obamas illuminate their evolving relationship with the Biden administration and the challenges they face.

Governor Gretchen Whitmer of Michigan discusses her bestselling book, sharing insights on leadership and her journey to earning the nickname 'Big Gretch' while taking on Trump. Comedian Jordan Klepper joins Illinois Governor JB Pritzker for a hilarious tour of Chicago, touching on history, pizza culture, and local spirits. The banter includes rumors of celebrity appearances at the DNC and the challenges of connecting with voters, peppered with humor and a celebration of Chicago's vibrant culture.

JB Pritzker, the Illinois governor making waves on the national stage, discusses his political ambitions and potential vice presidential candidacy. The conversation humorously connects the end of a local scholarship program to a memorable episode of 'The Office.' They also reflect on the vibrant yet overwhelming summer festival scene in Chicago, weighing the joys of communal gatherings against the fatigue of seasonal events. It's a candid look at politics and community life in the Windy City.

Vice President Kamala Harris discusses Donald Trump's controversial remarks questioning her racial identity at the NABJ convention. She emphasizes the need for respect and unity while condemning Trump's divisive rhetoric. Illinois Governor JB Pritzker joins the conversation, tackling the implications of Trump's comments on the GOP and civil rights. The duo highlights the importance of civic engagement and calls for a focus on policy debates over personal attacks leading into the elections.